Ethylene transposition: Ruthenium hydride catalyzed intramolecular trans -silylvinylation of internal alkynes

Shasha Liu; Jinbo Zhao; Lauren Kaminsky; Robert J. Wilson; Nadia Marino; Daniel A. Clark

doi:10.1021/ol5020027

Ethylene transposition: Ruthenium hydride catalyzed intramolecular trans -silylvinylation of internal alkynes

Shasha Liu, Jinbo Zhao, Lauren Kaminsky, Robert J. Wilson, Nadia Marino, Daniel A. Clark

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

19 Scopus citations

Abstract

A highly selective intramolecular trans-silylvinylation of internal alkynes catalyzed by RuHCl(CO)(SIMes)(PPh₃) has been accomplished. The use of methyl vinyl ketone as an additive increased the efficiency of this transformation. This process was used to successfully form five-, six-, and seven-membered oxasilacycles by a formal anti-exo-dig cyclization.

Original language	English (US)
Pages (from-to)	4456-4459
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	17
DOIs	https://doi.org/10.1021/ol5020027
State	Published - Sep 5 2014

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/ol5020027

Cite this

@article{6d26102393d944a59e641d97d6a3e140,

title = "Ethylene transposition: Ruthenium hydride catalyzed intramolecular trans -silylvinylation of internal alkynes",

abstract = "A highly selective intramolecular trans-silylvinylation of internal alkynes catalyzed by RuHCl(CO)(SIMes)(PPh3) has been accomplished. The use of methyl vinyl ketone as an additive increased the efficiency of this transformation. This process was used to successfully form five-, six-, and seven-membered oxasilacycles by a formal anti-exo-dig cyclization.",

author = "Shasha Liu and Jinbo Zhao and Lauren Kaminsky and Wilson, {Robert J.} and Nadia Marino and Clark, {Daniel A.}",

note = "Publisher Copyright: {\textcopyright} 2014 American Chemical Society.",

year = "2014",

month = sep,

day = "5",

doi = "10.1021/ol5020027",

language = "English (US)",

volume = "16",

pages = "4456--4459",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "17",

}

TY - JOUR

T1 - Ethylene transposition

T2 - Ruthenium hydride catalyzed intramolecular trans -silylvinylation of internal alkynes

AU - Liu, Shasha

AU - Zhao, Jinbo

AU - Kaminsky, Lauren

AU - Wilson, Robert J.

AU - Marino, Nadia

AU - Clark, Daniel A.

PY - 2014/9/5

Y1 - 2014/9/5

N2 - A highly selective intramolecular trans-silylvinylation of internal alkynes catalyzed by RuHCl(CO)(SIMes)(PPh3) has been accomplished. The use of methyl vinyl ketone as an additive increased the efficiency of this transformation. This process was used to successfully form five-, six-, and seven-membered oxasilacycles by a formal anti-exo-dig cyclization.

AB - A highly selective intramolecular trans-silylvinylation of internal alkynes catalyzed by RuHCl(CO)(SIMes)(PPh3) has been accomplished. The use of methyl vinyl ketone as an additive increased the efficiency of this transformation. This process was used to successfully form five-, six-, and seven-membered oxasilacycles by a formal anti-exo-dig cyclization.

UR - http://www.scopus.com/inward/record.url?scp=84908060552&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84908060552&partnerID=8YFLogxK

U2 - 10.1021/ol5020027

DO - 10.1021/ol5020027

M3 - Article

AN - SCOPUS:84908060552

SN - 1523-7060

VL - 16

SP - 4456

EP - 4459

JO - Organic Letters

JF - Organic Letters

IS - 17

ER -

Ethylene transposition: Ruthenium hydride catalyzed intramolecular trans -silylvinylation of internal alkynes

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this